Chemistry Heterocyclic Building Blocks Oxadiazoles

Oxadiazoles

Oxadiazoles belong to the azole family of heterocyclic aromatic compounds and have the molecular formula C2H2N2O. There exist four oxadiazole isomers, 1,2,3-isomer, 1,2,4-Oxadiazole, 1,2,5-oxadiazole, and 1,3,4-oxadiazole.

Several pharmaceutical drugs, including raltegravir, butalamine, fasiplon, oxolamine, and pleconaril, contain 1,2,4-oxadiazole, 1,2,5-oxadiazole, or 1,3,4-oxadiazole. The 1,2,3-isomer is prone to ring-opening and forms the diazoketone tautomer, but it can be found in the uncommon sydnone motif.

Oxadiazoles are used in two ways in pharmacology: as a crucial component of the pharmacophore or as a planar aromatic linker that positions substituents correctly and adjusts molecular properties.

There are various regioisomeric forms of oxadiazoles, which are organic heteroaromatic rings comprised of a five-membered structure with two nitrogen atoms and one oxygen atom.

Among the four isomers that exist, the 1,3,4-oxadiazole isomer is the most commonly utilized for diverse applications. The derivatives of 1,3,4-oxadiazole display a broad spectrum of biological properties, such as anti-cancer, anti-inflammatory, analgesic, anticonvulsant, and anti-HIV activities.

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1,2,4-oxadiazole 1,2,5-oxadiazole 1,3,4-oxadiazole 2,5-diphenyl-1,3,4-oxadiazole 2-phenyl-1,3,4-oxadiazole 3-phenyl-1,2,4-oxadiazole benzo[c][1,2,5]oxadiazole

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benzoxadiazole methyl-oxadiazole oxadiazo-pyridine oxadiazol-amide oxadiazol-one oxadiazole-carboxylate oxadiazole-carboxylic acid phenyl-oxadiazole

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Aromatic Heterocycles Benzimidazoles Isoxazoles Other Aromatic Heterocycles Piperidines Pyridazines Pyrrolidines Triazoles

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    5-(2-Fluorophenyl)-1,3,4-oxadiazole-2-thiol

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    A675151108413-51-097%

    5-(2-Fluorophenyl)-1,3,4-oxadiazole-2-thiol

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    Benzofuroxan

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    Benzofuroxan

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    2-(4-Chlorophenyl)-N-(4-(5-(furan-2-yl)-1,3,4-oxadiazol-2-yl)phenyl)acetamide

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    A1229371370854-75-498%

    2-(4-Chlorophenyl)-N-(4-(5-(furan-2-yl)-1,3,4-oxadiazol-2-yl)phenyl)acetamide

    $2035.00/100mg

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    2-(Chloromethyl)-5-methyl-1,3,4-oxadiazole

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    A9013973914-42-995%

    2-(Chloromethyl)-5-methyl-1,3,4-oxadiazole

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    4-(1H-Benzo[d]imidazol-2-yl)-1,2,5-oxadiazol-3-amine

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    A542473332026-86-598%

    4-(1H-Benzo[d]imidazol-2-yl)-1,2,5-oxadiazol-3-amine

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    2-Benzyl-5-(chloromethyl)-1,3,4-oxadiazole

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    A42230636646-13-695+%

    2-Benzyl-5-(chloromethyl)-1,3,4-oxadiazole

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    TH5427

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    A16033592253744-56-698%

    TH5427

    $1049.00/10mg

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    GSK269962A

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    A266066850664-21-098%

    GSK269962A

    $48.00/1mg

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    GSK-690693

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    A111141937174-76-098+%

    GSK-690693

    $605.00/100mg

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    3-Methyl-5-(piperazin-1-yl)-1,2,4-oxadiazole

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    A99273667869-92-595%

    3-Methyl-5-(piperazin-1-yl)-1,2,4-oxadiazole

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    Benzo[c][1,2,5]oxadiazole-4-carboxylic acid

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    A29313532863-21-198%

    Benzo[c][1,2,5]oxadiazole-4-carboxylic acid

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    5-(1-(3-Bromobenzyl)-5-methyl-1H-1,2,4-triazol-3-yl)-3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole

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    A19281021570494-48-298%

    5-(1-(3-Bromobenzyl)-5-methyl-1H-1,2,4-triazol-3-yl)-3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole

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    2-(3-Bromophenyl)-5-cyclopropyl-1,3,4-oxadiazole

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    A79220139959-43-897%

    2-(3-Bromophenyl)-5-cyclopropyl-1,3,4-oxadiazole

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    5-(Pyridin-3-yl)-1,3,4-oxadiazole-2-thiol

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    A5546023690-46-895%

    5-(Pyridin-3-yl)-1,3,4-oxadiazole-2-thiol

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    (S)-tert-Butyl (1-(5-mercapto-1,3,4-oxadiazol-2-yl)ethyl)carbamate

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    A6029141173685-53-497%

    (S)-tert-Butyl (1-(5-mercapto-1,3,4-oxadiazol-2-yl)ethyl)carbamate

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    2-(Benzo[d][1,3]dioxol-5-yl)-5-((3-fluoro-4-methoxybenzyl)thio)-1,3,4-oxadiazole

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    A1229387757198-76-898%

    2-(Benzo[d][1,3]dioxol-5-yl)-5-((3-fluoro-4-methoxybenzyl)thio)-1,3,4-oxadiazole

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    3-(Chloromethyl)-5-ethyl-1,2,4-oxadiazole

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    A59225683227-01-495%

    3-(Chloromethyl)-5-ethyl-1,2,4-oxadiazole

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    4-(1,2,4-Oxadiazol-3-yl)aniline

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    A46094959908-70-296%

    4-(1,2,4-Oxadiazol-3-yl)aniline

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    N-Methyl-N-phenyl-2-((5-phenyl-1,3,4-oxadiazol-2-yl)thio)acetamide

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    A1227426736950-05-398%

    N-Methyl-N-phenyl-2-((5-phenyl-1,3,4-oxadiazol-2-yl)thio)acetamide

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    5-(2-Iodophenyl)-3-methyl-1,2,4-oxadiazole

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    A10754821283108-04-295%

    5-(2-Iodophenyl)-3-methyl-1,2,4-oxadiazole

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